Compostos biologicamente ativos em invertebrados marinhos

ARTIGOS

Compostos biologicamente ativos em invertebrados marinhos

José Carlos de Freitas

Departamento de Fisiologia Geral - Instituto de Biociências, Universidade de São Paulo, São Paulo, SP, Brasil

SYNOPSIS

The author has reviewed the classification, the nomenclature and the ecological aspects of biologically active compounds, emphasizing the Freyvogel & Perret's (1973) concepts of venomous and poisonous organisms. The literature involving the phyla Annelida, Mollusca and Arthropoda was also reviewed. The author's pharmacological studies performed with the polychaete Eurytlioe camplanata, which revealed a dializable principle, active in the guinea pig's ileum and dorsal muscle ot polvchaete itself are also commented. This principle differs from Acetylcholine and Serotonin. Pharmacologically studies in the sea-hares (genus Aplysia) were also focused, including the author's contribution. In the glands os Aplysia brasiliana, namely the mid-gut-gland, the opaline gland and the purple gland, the author confirmed presence of cholinesters, which are discussed in the review. Toxicity of Arthropods are also discussed, mainly in decapod crustaceans. In some Brazilian crabs studies revealed a pharmacological activity of the gastric secretion expelled with an apparently defensive purpose and its ecological importance is focused in terms of the community. The relatively scarce studies of chemical ecology of marine organisms in Latin America and the importance of these studies were finally emphasized.

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Agradecimentos

Sou muito grato ao Prof. Dr. E.G. Mendes pela troca de idéias e revisão do manuscrito e ao Prof. Dr. Edmundo Nonato pela identificação da espécie Eurythoë complanata.

Bibliografia

ALCALA, A.G. & HALSTEAD, B.W. 1970 Human fatality due to ingestion of the crab Demania sp in the Philippines. Clinicai Toxicol., 3(4):609-611.

AXELROD, J. & SAAVEDRA, J.M. 1977 Octopamine. Nature, 265:501.

BAGNIS. R. 1970 A case of coconut crab poisoning. Clinical Toxicol., 3(4):585-588.

BASLOW, M.H. 1960 Marine pharmacology. A study of toxins and other biologically active substances of marine origin. Baltimore, Williams & Wilkins, 286p.

BASLOW, M.H. 1971 Marine toxins. Ann. Rev. Pharmacol. 11:447-454.

BAXTER, E.H.: MARR, A.G. & LANE, W.R. 1968 Immunity to the venon of the sea wasp, Chironex flexkeri. Toxicon, 6:45-50.

BERGMANN, W. & FEENEY, R.J. 1951 Contributions to the study of marine products. XXXII. The Nucleosides of sponges. I.J. Org. Chem., 16:981-987.

BLANKENSHIP, J.E.; LANGLAIS, P.J. & KITTREDGE, J.S. 1975 Identification of a cholinomimetic compound in the digestive gland of Aplysia californica. Comp. Biochem. Physiol., 57C:129-137

BROWER, L.P. & BROWER J.V.Z. 1964 Birds, butterflies, and plant poisons: a study in ecological chemistry. Zoológica, N.Y., 49:137-159.

BROWN Jr., W.L.; EISNER, T. & WHITTAKER, R.H. 1970 Allomones and kairomones: transpecific chemical messengers. Bioscience, 20:21.

BUCHERL, W. & BUCKLEY. E.E. 1971 Venomous animals and their venoms, v. 3 Venomous invertebrates. New York, Academic Press, 537p.

COURVILLE, D.A.; HALSTEAD, B.W. & HESSEL, D.W. 1958 Marine biotoxins: isolation and properties. Chem. Rev., 58:235-248.

DAY, J.H. 1967 Polychaeta of Southern Africa, Part I. Errantia. London. Brit. Mus. (Nat. Hist.), 458p.

DUBOIS, R. 1903 Sur le venin de la glande à pourpre des Murex. Apud RUSSELL, F.E. 1971.

ENDEAN, R. 1972 Aspects of molluscan pharmacology. In: FLOR-KIN, M. & SCHEER, N.Y., ed. Chemical zoology. Mollusca, 7. New York, Academic Press, p.421-466.

ERSPAMER, V. 1948 Observazioni preliminari chimiche e farmacologiche, sulla murexina. Experientia, 4:226-228.

ERSPAMER, V. & BENATI, O. 1953 Identification pf murexine as beta (imidazolyl-(4)-acryl-choline. Science, 117:161-162.

ERSPAMER, V. & GLASSER, A. 1957 The pharmacological actions of murexina (Urocanylcholine). Brit. J. Pharmacol. Chemother., 12:176-184.

FEDER, H.M. 1967 Apud MACKIE, A.M. 1975.

FLORKIN, M. 1966 Aspects moleculaires de l'adaptation et de la phylogénie. Paris, Masson, 258p.

FLURY, F. 1915 Uber das Aplysiengift. Apud RUSSELL, F.E 1971.

FOX, H.M. 1924 Apud MACKIE, A.M. 1975.

FREITAS, J.C. 1977 Ocorrência de esteres de cotina em Aplysia brasiliana Rang, 1828 (Mollusca, Gastropoda, Opisthobranchia). 2ª SEMANA DE SEMINÁRIOS DE BIOLOGIA MARINHA, São Sebastião, S.P. - Anais Acad. bras. Ciênc. (No prelo).

FREY VOGEL, T.A. & PERRET, B.A. 1973 Notes on toxinology. Experientia, 29(11):1317-1452.

GARTH, J.S. 1972 Demania toxica, a new species of poisonous crab from the Philippines. Micronesica, 7(1/2):179-183.

GHIRETTI, F. 1960 Toxicity of octopus saliva against Crustacea. Ann. N.Y. Acad. Sci., 90:726-741.

GONZALEZ, R.B. & ALCALA, A.C. 1977 Fatalities from crab poisoning on Negros Island, Philippines. Toxicon, 15:169-170.

GRANT, P.T. & MACKIE, A.M. 1977 Drugs from the sea: fact or fantasy? Nature, 267:786-788.

HALSTEAD, B.W. 1959 Dangerous marine animals. Cambridge, Cornell marit. Press. 146p.

HALSTEAD, B.W. 1965 Poisonous and venomous marine animals of the world. I. Invertebrates. Washington, U. S. Gov. Printing Office, 994p.

HALSTEAD, B.W. 1976 Shellfish emotionalism. Clinical Toxicology, 9(1):1-2.

HASHIMOTO, Y.; KONOSU, S.; INOUE, A. & NOGUCHI, T. 1967 Ocurrence of toxic crabs in Ryukyu and Amami Islands. Toxicon, 5:85-90.

HASHIMOTO, Y.; KONOSU, S.; INOUE, A.; SAISHO, T. & MIYAKE, S. 1969 Screening of toxic crabs in the Ryukyu and Amami Islands. Bull. Jap. Soc. scient. Fish., 35 (1):83-87.

HIGA, T. & SCHEWER, P.T. 1975 Antitumor activity in mice of tentacles of two tropical sea annelids. Apud GRANT, PIT. & MACKIE, A.M. 1977.

HOWE, N.R. & SHEIKH, Y.M. 1975 Anthopleurine. A sea-anemone alarm pheromone. Science, 189:386-388.

HUANG, C.L. & MIR, G.N. 1972 Pharmacological investigation of salivary gland of Thais haemastoma (Clench). Toxicon, 10:111-117.

INOUE, A.; NOGUCHI. T.; KONOSU, S. & HASHIMOTO. Y. 1968 A new toxic crab, A tergatis floridus. Toxicon, 6:119-123.

JULLIEN, A. 1940 Variations dans les temps de la teneur des ex-. traits de glande à pourpre en substances actives sur le muscle de sangsue. Cr. Séanc. Soc. Biol., 123:524-527.

KANDEL, E.R. 1976 Cellular basis of behaviour. An introduction to behavioral neurobiology. San Francisco, W.H. Freeman, 727p.

KARLSON, P. & LUSCHER, M. 1959 Pheromones: a new term for a class of biologically active substances. Nature, Lond., 183:55-56.

KAY, E.A. 1969 The aplysiidae of the Hawaiian Islands. Apud WATSON, M. 1973.

KITTREDGE, J.S.; TAKAHASHI, F.T.; LINDSEY, J. & LASKER, R. 1974 Chemical signals in the sea:marine allelochemics and evolution. Bull. Fish. Wildl. Serv. U.S.,72: 1-12.

KOHN, AJ.; SAUNDERS, P.R. & WIENER'S. 1960 Preliminary studies on the venom of the marine snail Conus. Ann. N.Y. Acad. Sci., 90:706-725.

KONOSU, S.; INOUE, A.; NOGUCHI, T. & HASHIMOTO, Y. 1968 Comparison of crab toxin with Saxitoxin and Tetrodotoxin. Toxicon, 6:113-117.

KONOSU. S INOUE, A.: NOGUCHI. T. & HASHIMOTO Y. 1969 A further examination on the toxicity of three species of xanthid crab. Bull. Jap. Soc. scient. Fish., 35(1):88-92.

LÉVY, R. 1923 Sur la toxicité des tissus de la sacculine (Sacculina carcini Thomp.)vis-á-vis du crabe (Carcinus maenas Penn.) et sur la recherche de reactions d'immunité chez ce dernier. Bull. Soc. Zool. Fr., 48:291-294.

MACKIE, A.M., 1975. Chemoreception. In: MALINS, D.C. & SARGENT, J.R., ed. - Biochemical and biophysical perspectives in marine biology, II. New York, Academic Press, 359p.

MACKIE, A.M. & GRANT, P.T. 1974 Interspecies and intraspecies chemoreception by marine invertebrates. In: GRANT, P.T. & MACKIE, A.M., Chemoreception in marine organisms. London. Academic Press, 295p.

MARGALEF, F., 1974. Ecologia. Barcelona, Ediciones Omega, 951p.

MARTIN, D.F. & PADILLA, G.M., 1973 Marine pharmacognosy. Action of marine biotoxins at the cellular level. New York. Academic Press, 317p.

MURAKAMI, S.; TAKEMOTO, T.; TEI, Z. & DAIGO, K. 1955 Effective principles of Digenea simples XIII. Structure of kainic acid. Apud MARTIN, D.F. & PADILLA, G.M., ed. 1973.

NARAHASHI, T. 1973 Mode of action of Nereistoxin on excitable tissues. In: MARTIN, D.F. & PADILLA, E.M.,ed. 1973.

NIGRELLI, R.F. STEMPIEN, Jr. M.F.; RUGGIERI, G.D.; LIGUORI, V.R. & CECIL, J.T. 1967 Substances of potencial biomedical importance from organisms. Federation Proc, 26(4):1197-1205.

NOGUCHI, T; KONOSU, S. & HASHIMOTO, Y. 1969. Identity of the crab toxin with Saxitoxin. Toxicon, 7:323-326.

QUILLIAM, J.P. 1957 The mechanism of action of Murexine on neuromuscular transmission in the frog. Br. J. pharmac. Chemother., 12:388-392.

RASKOVÁ, H., ed. 1971 Pharmacology and toxicology of naturally occurring toxins. IUPHAR, v.2. Oxford, Pergamon Press. 299p.

ROSEGHINI, M; ERSPAMER, V.; RAMORINO, M.L. & GUTIERREZ, J.E. 1970 Choline esters, their precursors and metabolites in the hypobranchial gland of prosobranchiate molluscs, Concholepas concholepas and Thais chocolata. Eur. J. Biochem., 12:468-473.

ROSEGHINI, M. & FICHMAN, M. 1973 Choline esters and imidazole acids in extracts of the hypobranchial gland of Thais haemastoma. Comp. gen. Pharmacol., 4:251-257.

RUGGIERI, G.D., 1976 Drugs from the sea. Marine organisms with novel chemical constituents are excellent sources of new drugs Science, 194:491-497.

RUSSELL, F.E., 1965. Marine toxins and venomous and poisonous marine animals. Adv. mar. Biol., 3:284 p.

RUSSELL, F.E. 1967 Comparative pharmacology of some animal toxins. Federation Proc, 26(4):1206-1224.

RUSSELL, F.E. 1971 Pharmacology of toxins of marine organisms. In: RASKOVÁ, H. ed. 1971.

RUSSELL-HUNTER. W.D. 1968 A biology of lower invertebrates. New York, MacMillan, 181p.

RUSSELL, F.E. & SAUNDERS, P.R. 1967 Animal toxins. Oxford, Pergamon Press, 428p.

SASNER, Jr., J.J., 1973 Comparative studies on algal toxins. In:MARTIN, D.F. & PADILLA, G..M., ed. 1973.

SAWAYA, P. 1966 Toxic marine invertebrates. Venomous and noxious fisches of fresh water. Mem. Inst. Butantan,33(1):31-34.

SCHEUER, P.J. 1964 The chemistry of toxins isolated from some marine organisms. Forthschr. Chem. Org. NatStoff, 22:265-278.

SCHEUER, P.J. 1977 Chemical communication of marine invertebrates. Bioscience, 27(10):664-668.

SOMMER, H., 1932. The occurrence of the paralytic shellfish poison in the common sand crab. Science, 76:574-575.

SONDHEIMER, E. & SIMEONE, J.B. 1970 Chemical ecology. Apud KITTREDGE, J.S.; TAKAHASHI, F.T.; LINDSEY, J. & LASKER, R. 1974.

SOUTHCOTT, R.V.,1970. Human injuries from invertebrate animals in the Australian Seas. Clinical Toxicol, 3(4):617-636.

STALLARD, M.O. & FAULKNER, D.J., 1974. Chemical constituents of the digestive gland of the sea hare Aplysia californica. - I. Importance of diet. Comp. Biochem. Physiol., 49B:25-35.

TABRAH, F.L.; KASHIWAGI, M. & NORTON, T.R. 1970 Antitumor activity in mice of tentacles of two tropical sea annelids. Science, 170:181-183.

THRISHNANANDA, M.; TUCHINDA, D.; YIPINSOI, T. & OONSOMBAT. P. 1966 Poisoning following the ingestion of the horseshoe crab (Carcinoscorpius rotundicauda): Report of four cases in Thailand. Apud BASLOW, M.H. 1960.

TWAROG, B.M.; HIDAKA, T. & YAMAGUCHI, H. 1972 Resistance to Tetrodotoxin and Saxitoxin in nerves of bivalve molluscs. A possible correlation with paralytic shellfish poisoning. Toxicon, 10:213-218.

VICENTE, D. & JULLIEN, A. 1938 Richesse de la glande a pourpre des Murex en esters de la choline, Cr. Séanc. Soc. Biol., 127:1506.

WATSON, M., 1973. Midgut gland toxins of Hawaiian sea hares. I. Isolation and preliminary toxicological observation. Toxicon, 11:259-267.

WATSON, M. & RAYNER, M.D. 1973 Midgut gland toxins of Hawaiian sea hares. II. A preliminary pharmacological study. Toxicon. 11:269-276.

WHITTAKER, V.P., 1960 Pharmacologically active choline esters in marine gastropods. Ann. N.Y. Acad. Sci., 90:695-705.

WHITTAKER, R.H. & FEENY, P.P. 1971 Allelochemics: chemical interaction between species. Science, 171:757-770.

WINKLER, L.R. 1961 Preliminary tests of the toxin extracted from Californian sea hares, of the genus Aplysia. Pacific Sc., 15:211-214.

WINKLER, L.R. 1969 Distribution of organic brominc compounds in Aplysia californica Cooper, 1963. Veliger, 11:268-271

WINKLER, L.R.; TTLTON, B.E. & HARSMGE, M.G. 1962 A cholinergic agent extracted from sea hares, Arch. Int. Pharmacodyn., 137(1/2):76-83.

YALDWYN, J.C. 1965. Blistering from bristle worm. Aust. Nat. Hist.,15:86.

• AXELROD, J. & SAAVEDRA, J.M. 1977 Octopamine. Nature, 265:501.
• BAGNIS. R. 1970 A case of coconut crab poisoning. Clinical Toxicol., 3(4):585-588.
• BASLOW, M.H. 1960 Marine pharmacology. A study of toxins and other biologically active substances of marine origin. Baltimore, Williams & Wilkins, 286p.
• BASLOW, M.H. 1971 Marine toxins. Ann. Rev. Pharmacol. 11:447-454.
• BAXTER, E.H.: MARR, A.G. & LANE, W.R. 1968 Immunity to the venon of the sea wasp, Chironex flexkeri. Toxicon, 6:45-50.
• BERGMANN, W. & FEENEY, R.J. 1951 Contributions to the study of marine products. XXXII. The Nucleosides of sponges. I.J. Org. Chem., 16:981-987.
• BLANKENSHIP, J.E.; LANGLAIS, P.J. & KITTREDGE, J.S. 1975 Identification of a cholinomimetic compound in the digestive gland of Aplysia californica. Comp. Biochem. Physiol., 57C:129-137
• BROWER, L.P. & BROWER J.V.Z. 1964 Birds, butterflies, and plant poisons: a study in ecological chemistry. Zoológica, N.Y., 49:137-159.
• BROWN Jr., W.L.; EISNER, T. & WHITTAKER, R.H. 1970 Allomones and kairomones: transpecific chemical messengers. Bioscience, 20:21.
• BUCHERL, W. & BUCKLEY. E.E. 1971 Venomous animals and their venoms, v. 3 Venomous invertebrates. New York, Academic Press, 537p.
• COURVILLE, D.A.; HALSTEAD, B.W. & HESSEL, D.W. 1958 Marine biotoxins: isolation and properties. Chem. Rev., 58:235-248.
• DAY, J.H. 1967 Polychaeta of Southern Africa, Part I. Errantia. London. Brit. Mus. (Nat. Hist.), 458p.
• ENDEAN, R. 1972 Aspects of molluscan pharmacology. In: FLOR-KIN, M. & SCHEER, N.Y., ed. Chemical zoology. Mollusca, 7. New York, Academic Press, p.421-466.
• ERSPAMER, V. 1948 Observazioni preliminari chimiche e farmacologiche, sulla murexina. Experientia, 4:226-228.
• ERSPAMER, V. & BENATI, O. 1953 Identification pf murexine as beta (imidazolyl-(4)-acryl-choline. Science, 117:161-162.
• ERSPAMER, V. & GLASSER, A. 1957 The pharmacological actions of murexina (Urocanylcholine). Brit. J. Pharmacol. Chemother., 12:176-184.
• FLORKIN, M. 1966 Aspects moleculaires de l'adaptation et de la phylogénie. Paris, Masson, 258p.
• FREITAS, J.C. 1977 Ocorrência de esteres de cotina em Aplysia brasiliana Rang, 1828 (Mollusca, Gastropoda, Opisthobranchia). 2Ş SEMANA DE SEMINÁRIOS DE BIOLOGIA MARINHA, São Sebastião, S.P.
• - Anais Acad. bras. Ciênc. (No prelo).
• FREY VOGEL, T.A. & PERRET, B.A. 1973 Notes on toxinology. Experientia, 29(11):1317-1452.
• GARTH, J.S. 1972 Demania toxica, a new species of poisonous crab from the Philippines. Micronesica, 7(1/2):179-183.
• GHIRETTI, F. 1960 Toxicity of octopus saliva against Crustacea. Ann. N.Y. Acad. Sci., 90:726-741.
• GONZALEZ, R.B. & ALCALA, A.C. 1977 Fatalities from crab poisoning on Negros Island, Philippines. Toxicon, 15:169-170.
• GRANT, P.T. & MACKIE, A.M. 1977 Drugs from the sea: fact or fantasy? Nature, 267:786-788.
• HALSTEAD, B.W. 1959 Dangerous marine animals. Cambridge, Cornell marit. Press. 146p.
• HALSTEAD, B.W. 1965 Poisonous and venomous marine animals of the world. I. Invertebrates. Washington, U. S. Gov. Printing Office, 994p.
• HALSTEAD, B.W. 1976 Shellfish emotionalism. Clinical Toxicology, 9(1):1-2.
• HASHIMOTO, Y.; KONOSU, S.; INOUE, A. & NOGUCHI, T. 1967 Ocurrence of toxic crabs in Ryukyu and Amami Islands. Toxicon, 5:85-90.
• HASHIMOTO, Y.; KONOSU, S.; INOUE, A.; SAISHO, T. & MIYAKE, S. 1969 Screening of toxic crabs in the Ryukyu and Amami Islands. Bull. Jap. Soc. scient. Fish., 35 (1):83-87.
• HOWE, N.R. & SHEIKH, Y.M. 1975 Anthopleurine. A sea-anemone alarm pheromone. Science, 189:386-388.
• HUANG, C.L. & MIR, G.N. 1972 Pharmacological investigation of salivary gland of Thais haemastoma (Clench). Toxicon, 10:111-117.
• INOUE, A.; NOGUCHI. T.; KONOSU, S. & HASHIMOTO. Y. 1968 A new toxic crab, A tergatis floridus. Toxicon, 6:119-123.
• JULLIEN, A. 1940 Variations dans les temps de la teneur des ex-. traits de glande à pourpre en substances actives sur le muscle de sangsue. Cr. Séanc. Soc. Biol., 123:524-527.
• KANDEL, E.R. 1976 Cellular basis of behaviour. An introduction to behavioral neurobiology. San Francisco, W.H. Freeman, 727p.
• KARLSON, P. & LUSCHER, M. 1959 Pheromones: a new term for a class of biologically active substances. Nature, Lond., 183:55-56.
• KITTREDGE, J.S.; TAKAHASHI, F.T.; LINDSEY, J. & LASKER, R. 1974 Chemical signals in the sea:marine allelochemics and evolution. Bull. Fish. Wildl. Serv. U.S.,72: 1-12.
• KOHN, AJ.; SAUNDERS, P.R. & WIENER'S. 1960 Preliminary studies on the venom of the marine snail Conus. Ann. N.Y. Acad. Sci., 90:706-725.
• KONOSU, S.; INOUE, A.; NOGUCHI, T. & HASHIMOTO, Y. 1968 Comparison of crab toxin with Saxitoxin and Tetrodotoxin. Toxicon, 6:113-117.
• KONOSU. S INOUE, A.: NOGUCHI. T. & HASHIMOTO Y. 1969 A further examination on the toxicity of three species of xanthid crab. Bull. Jap. Soc. scient. Fish., 35(1):88-92.
• LÉVY, R. 1923 Sur la toxicité des tissus de la sacculine (Sacculina carcini Thomp.)vis-á-vis du crabe (Carcinus maenas Penn.) et sur la recherche de reactions d'immunité chez ce dernier. Bull. Soc. Zool. Fr., 48:291-294.
• MACKIE, A.M., 1975. Chemoreception. In: MALINS, D.C. & SARGENT, J.R., ed. - Biochemical and biophysical perspectives in marine biology, II. New York, Academic Press, 359p.
• MACKIE, A.M. & GRANT, P.T. 1974 Interspecies and intraspecies chemoreception by marine invertebrates. In: GRANT, P.T. & MACKIE, A.M., Chemoreception in marine organisms. London. Academic Press, 295p.
• MARGALEF, F., 1974. Ecologia. Barcelona, Ediciones Omega, 951p.
• MARTIN, D.F. & PADILLA, G.M., 1973 Marine pharmacognosy. Action of marine biotoxins at the cellular level. New York. Academic Press, 317p.
• NARAHASHI, T. 1973 Mode of action of Nereistoxin on excitable tissues. In: MARTIN, D.F. & PADILLA, E.M.,ed. 1973.
• NIGRELLI, R.F. STEMPIEN, Jr. M.F.; RUGGIERI, G.D.; LIGUORI, V.R. & CECIL, J.T. 1967 Substances of potencial biomedical importance from organisms. Federation Proc, 26(4):1197-1205.
• NOGUCHI, T; KONOSU, S. & HASHIMOTO, Y. 1969. Identity of the crab toxin with Saxitoxin. Toxicon, 7:323-326.
• QUILLIAM, J.P. 1957 The mechanism of action of Murexine on neuromuscular transmission in the frog. Br. J. pharmac. Chemother., 12:388-392.
• RASKOVÁ, H., ed. 1971 Pharmacology and toxicology of naturally occurring toxins. IUPHAR, v.2. Oxford, Pergamon Press. 299p.
• ROSEGHINI, M; ERSPAMER, V.; RAMORINO, M.L. & GUTIERREZ, J.E. 1970 Choline esters, their precursors and metabolites in the hypobranchial gland of prosobranchiate molluscs, Concholepas concholepas and Thais chocolata. Eur. J. Biochem., 12:468-473.
• ROSEGHINI, M. & FICHMAN, M. 1973 Choline esters and imidazole acids in extracts of the hypobranchial gland of Thais haemastoma. Comp. gen. Pharmacol., 4:251-257.
• RUGGIERI, G.D., 1976 Drugs from the sea. Marine organisms with novel chemical constituents are excellent sources of new drugs Science, 194:491-497.
• RUSSELL, F.E., 1965. Marine toxins and venomous and poisonous marine animals. Adv. mar. Biol., 3:284 p.
• RUSSELL, F.E. 1967 Comparative pharmacology of some animal toxins. Federation Proc, 26(4):1206-1224.
• RUSSELL, F.E. 1971 Pharmacology of toxins of marine organisms. In: RASKOVÁ, H. ed. 1971.
• RUSSELL-HUNTER. W.D. 1968 A biology of lower invertebrates. New York, MacMillan, 181p.
• RUSSELL, F.E. & SAUNDERS, P.R. 1967 Animal toxins. Oxford, Pergamon Press, 428p.
• SASNER, Jr., J.J., 1973 Comparative studies on algal toxins. In:MARTIN, D.F. & PADILLA, G..M., ed. 1973.
• SAWAYA, P. 1966 Toxic marine invertebrates. Venomous and noxious fisches of fresh water. Mem. Inst. Butantan,33(1):31-34.
• SCHEUER, P.J. 1964 The chemistry of toxins isolated from some marine organisms. Forthschr. Chem. Org. NatStoff, 22:265-278.
• SCHEUER, P.J. 1977 Chemical communication of marine invertebrates. Bioscience, 27(10):664-668.
• SOMMER, H., 1932. The occurrence of the paralytic shellfish poison in the common sand crab. Science, 76:574-575.
• SOUTHCOTT, R.V.,1970. Human injuries from invertebrate animals in the Australian Seas. Clinical Toxicol, 3(4):617-636.
• STALLARD, M.O. & FAULKNER, D.J., 1974. Chemical constituents of the digestive gland of the sea hare Aplysia californica. - I. Importance of diet. Comp. Biochem. Physiol., 49B:25-35.
• TABRAH, F.L.; KASHIWAGI, M. & NORTON, T.R. 1970 Antitumor activity in mice of tentacles of two tropical sea annelids. Science, 170:181-183.
• TWAROG, B.M.; HIDAKA, T. & YAMAGUCHI, H. 1972 Resistance to Tetrodotoxin and Saxitoxin in nerves of bivalve molluscs. A possible correlation with paralytic shellfish poisoning. Toxicon, 10:213-218.
• VICENTE, D. & JULLIEN, A. 1938 Richesse de la glande a pourpre des Murex en esters de la choline, Cr. Séanc. Soc. Biol., 127:1506.
• WATSON, M., 1973. Midgut gland toxins of Hawaiian sea hares. I. Isolation and preliminary toxicological observation. Toxicon, 11:259-267.
• WATSON, M. & RAYNER, M.D. 1973 Midgut gland toxins of Hawaiian sea hares. II. A preliminary pharmacological study. Toxicon. 11:269-276.
• WHITTAKER, V.P., 1960 Pharmacologically active choline esters in marine gastropods. Ann. N.Y. Acad. Sci., 90:695-705.
• WHITTAKER, R.H. & FEENY, P.P. 1971 Allelochemics: chemical interaction between species. Science, 171:757-770.
• WINKLER, L.R. 1961 Preliminary tests of the toxin extracted from Californian sea hares, of the genus Aplysia. Pacific Sc., 15:211-214.
• WINKLER, L.R. 1969 Distribution of organic brominc compounds in Aplysia californica Cooper, 1963. Veliger, 11:268-271
• WINKLER, L.R.; TTLTON, B.E. & HARSMGE, M.G. 1962 A cholinergic agent extracted from sea hares, Arch. Int. Pharmacodyn., 137(1/2):76-83.
• YALDWYN, J.C. 1965. Blistering from bristle worm. Aust. Nat. Hist.,15:86.

Datas de Publicação

• Publicação nesta coleção
  06 Jun 2012
• Data do Fascículo
  1980